Celebrity Cross-Dressers Trivia Quiz

Answer:

Robin Williams played a divorced dad that created the female character of "Mrs. Doubtfire" in the same-named movie of 1993. This role and Williams' part as a gay man in "The Birdcage" (1996) illustrate his willingness to popularize non-traditional gender roles.

Tony Curtis (and Jack Lemmon) played male musicians that dressed as women to hide out in an all-girls band in "Some Like it Hot" (1959). Marilyn Monroe is a member of the band, making it difficult for Tony and Jack's characters to disguise their attraction to Marilyn.

John Travolta played the female character Edna Turnblad in the 2007 musical film "Hairspray". The character of Edna was also played by men in the original 1988 film (Harris Milstead, AKA Divine) and the 2002 musical (Harvey Fierstein).

Patrick Swayze played drag queen Vida Boheme in the 1995 file "To Wong Foo, Thanks for Everything! Julie Newmar". Wesley Snipes and John Leguizamo also starred as drag queens.

Jared Leto won a Best Supporting Actor Oscar playing the transgender woman Rayon in the 2013 movie "Dallas Buyer's Club". Leto lost over 30 pounds for the role, shaved his eyebrows, and refused to break character during filming, all of which lent veracity to his portrayal.

Tyler Perry created and portrayed Mabel Earlene "Madea" Simmons in thirteen Madea movies were made between 2005 through 2025, with more on the horizon.

Hilary Swank won a Best Actress Oscar portraying real-life trans man Brandon Teena in "Boys Don't Cry" (1999). Swank portrayed Teena's struggles hiding his identity in a violent world, and she honored his courage and legacy in her Oscar and Golden Globe acceptance speeches.

Linda Hunt won a Best Supporting Actress Oscar for portraying real-life male journalist Billy Kwan in "The Year of Living Dangerously" (1982). Linda became the first person to win an Oscar playing a character of the opposite sex.

Cate Blanchett dressed as a man and played the character Jude Quinn, reflecting a period of Bob Dylan's life, in the 2007 Dylan bio-pic "I'm Not There". The character Quinn represented Dylan's transition in the mid-60s from folk to rock music.

Julie Andrews played an out-of-work actress (Victoria Grant) who pretends to be a man (Victor Grazinski) and lands a role as a female impersonator in "Victor/Victoria" (1982). Besides the comedic angle, this also illustrates how men may have a more assured path to success in Hollywood than do women.